Shelter Island Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Welcome To The Beach. Driftwood beach hut with handwritten welcome sign. Port Crescent State Park. Port Austin, Michigan.

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Crescent Beach.

Find hotels in Menantic Creek

Find the Best Shelter Island Vacation Packages

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is ₩948,431 per night from May 31 to Jun 1
₩948,431
₩1,300,295 total
May 31 - Jun 1
includes taxes & fees
8.4/10 Very Good! (783 reviews)
"Wonderful stay. Appreciated the staffs attention and service when needed. They made the experience even better for my husband and I."

Reviewed on May 23, 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is ₩362,984 per night from Jun 1 to Jun 2
₩362,984
₩444,442 total
Jun 1 - Jun 2
includes taxes & fees
9.2/10 Wonderful! (1,350 reviews)
"We stayed at Montauk Manor the week before Memorial Day. The weather was beautiful, and we did a lot of hiking in the area, but one of my favorite trails is right behind the hotel. If you walk behind the tennis courts, it opens up into a trail around the Fort Hill Cemetery and there is an abundance ..."

Reviewed on May 24, 2026

Montauk Manor
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is ₩133,220 per night from Jun 7 to Jun 8
₩133,220
₩153,205 total
Jun 7 - Jun 8
includes taxes & fees
8/10 Very Good! (1,008 reviews)
"The mold was seen visible in the bathroom and the floors were not clean. Old furniture and asked for a rebate to no avail. Was told the property was updated. Beds are old and furniture is not new. TV has very few stations. Was not satisfied at all."

Reviewed on May 25, 2026

Pier Blue Inn Old Saybrook - Essex
See all 4,799 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Shelter Island

Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Havens House

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.